3-Pyridinecarboxaldehyde → 4,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-alpha-(3-pyridinyl)-2-pyrimidine-ethanol

HRID 1742604

Reaktionsgleichung

Reaktionsgleichung von HRID 1742604
C([Li])CCC.[CH3:6][C:7]([C:10]1[C:15]([O:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:13]=[C:12]([CH3:27])[N:11]=1)([CH3:9])[CH3:8].[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH:34]=[O:35])[CH:29]=1>C1COCC1>[CH3:9][C:7]([C:10]1[C:15]([O:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:13]=[C:12]([CH2:27][CH:34]([C:30]2[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=2)[OH:35])[N:11]=1)([CH3:6])[CH3:8]

Komponenten

5

Edukt 3

HCID 103713-PyridinecarboxaldehydeHCID 199229904,6-Ditert-butyl-5-[(2-methoxyethoxy)methoxy]-2-methylpyrimidineHCID 178418339Butyllithium

Produkt 1

HCID 190071464,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-alpha-(3-pyridinyl)-2-pyrimidine-ethanolAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

n-Butyllithium (1.5 mL of 1.6M solution in hexane, 2.4 mmol) is added dropwise to a solution of 4,6-bis (1,1-dimethylethyl)-5-[(2-methoxyethoxy) -methoxy]-2-methylpyrimidine (750 mg, 2.4 mmol) in dry THF (12 mL) at 0° C. under an atmosphere of dry nitrogen. The reaction mixture is stirred at room temperature for 30 minutes and then cooled to -78° C. A solution of pyridine 3-carboxaldehyde (250 mg, 2.4 mmol) in dry THF (1 mL) is added dropwise. The reaction mixture is stirred at room temperature for 3 hours and then is quenched by the addition of saturated aqueous ammonium chloride. The product is extracted into ether. The organic layer is dried (MgSO4) and evaporated to give crude 4,6-bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-α-(3 -pyridinyl)-2-pyrimidineethanol (500 mg, 50%) which is not further purified, but used directly in the next reaction.

Aufarbeitung

  1. temperaturecooled to -78° C
  2. stirringThe reaction mixture is stirred at room temperature for 3 hours
  3. customis quenched by the addition of saturated aqueous ammonium chloride
  4. extractionThe product is extracted into ether
  5. dry with materialThe organic layer is dried (MgSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7ea468ee44864125bf27e0b19c4f6992
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05340815

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